413595-06-9

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 104-87-0 4-methyl-benzaldehyde 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 

Relevant academic research and scientific papers

Spectral, catalytic, and antifungal studies of ruthenium(II) chalcone complexes

Reactions of [RuHCl(CO)(B)(EPh3)2] (B = EPh3 or Py; E = P or As) and chalcones in benzene with equal molar ratio led to the formation of new complexes of the type [RuCl(CO)(EPh3)(B)(L1-4)] (B = PPh3, AsPh3 or Py; E = P or As; L = chalcone). The new complexes have been characterized by analytical and spectroscopic (IR-, electronic, 1H-, 31P-, and 13C-NMR) data. Based on these data, an octahedral structure has been assigned for all the complexes. The chalcones are monobasic bidentate (O,O) donors and coordinate to ruthenium via phenolic and carbonyl oxygen. The new complexes exhibit efficient catalytic activity for the transfer hydrogenation of carbonyl compounds. Antifungal properties of the ligands and their complexes have been examined and compared with standard Bavistin.

Reaction of heteroaryl hydrazines with 3-Cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones: Synthesis of some novel pyrazolines and their iodine(III) mediated conversion to corresponding pyrazoles

A series of some novel 5-aryl-3-(4-hydroxy-6-methyl-2H-pyran-2-oxo-3-yl)-1-heteroaryl pyrazolines have been prepared by the reaction of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones i.e., chalcone analogues of dehydroacetic acid (DHA) with various heteroaryl hydrazines and converted to corresponding pyrazoles with iodobenzene diacetate in good yields.

Regioselective three component domino synthesis of polyhydrospiro[indoline-3,3'-pyrrolizine]-2-one via [3+2] Cycloaddition reaction

In present work, we have reported the synthesis and characterisation of novel hexahydrospiro[indoline-3,3′-pyrrolizine]-2-one derivatives in good to excellent yields via [3+2] cycloaddtion reaction in regioselective manner. These compounds were synthesized via multicomponent reaction of substituted 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-one, isatin, L-proline at room temperature. All the synthesized hexahydrospiro molecules were characterized by 1H and 13C NMR, IR spectra, mass spectra and elemental analysis. Regioselectivity in synthesized molecules were also explained on the basis of secondary orbital interactions. A simple and facile methodology is developed which has great importance in synthetic chemistry.

Synthesis and in vitro evaluation of substituted 3-cinnamoyl-4-hydroxy-pyran-2-one (CHP) in pursuit of new potential antituberculosis agents

Tuberculosis is an ever-evolving infectious disease that urgently needs new drugs. In the search for new antituberculosis agents, a library of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones (CHPs) (2a-2y) was synthesized and evaluated against a standard virulent laboratory strain of Mycobacterium tuberculosis H37Rv. Out of 25 compounds, 11, 5, 7 and 2 (2a and 2u) showed least, moderate, good and appreciable activities, respectively, based on minimum inhibitory concentrations (MICs). Both 2a and 2u exhibited an MIC value of 4 μg ml-1, which was close to those of standard antituberculosis drugs ethambutol, streptomycin and levofloxacin. Neither 2a nor 2u showed any activity against Gram-positive or Gram-negative bacteria and even against non-tuberculous mycobacterium, i.e. Mycobacterium smegmatis. Thus, like the antituberculosis drugs rifampicin, isoniazid and pretomanid, they are highly TB specific. All the pyrone-based chalcones showed no recognizable level of cytotoxicity against normal human kidney cell line (HEK-293) up to 80 μM concentration and 11 exhibited an IC50 ≤ 100 μM (highest tested concentration). On further investigation, both 2a and 2u proved to be nontoxic against four human cell lines but 2a proved to be a better choice as it did not reach IC50 even at 100 μM (highest tested concentration) while the IC50 of 2u was around 80 μM. In conclusion, our results demonstrate that 2a is specific against M. tuberculosis with no appreciable toxicity; its activity matches that of some clinically approved antituberculosis drugs and it therefore merits further evaluation.

Regioselective synthesis of some new 5-(4-aryl-2-oxobut-3- enyl)-3-methyl-1-(6-substituted benzothiazol-2- yl)pyrazoles from aryloct-7-en-2,4,6-triones

Dehydroacetic acid (DHA) and its derivatives find wide applications in synthetic organic chemistry. The 8-aryloct-7-en-2,4,6-triones (DHA-triones), which are accessible by a multistep procedure commencing from the commercially available DHA, on reaction with 6-substituted benzothiazolylhydrazines led to regioselective synthesis of several new 5-(4-aryl-2-oxobut-3-enyl)-3-methyl-1-(6-substituted benzothiazol-2-yl)pyrazoles.